vintage

Dating Fails Dating Fails
Favorite

Love for Some

bondage kinky love tied up vintage We Are Dating - 5415070208
By Unknown
  • -
  • Vote
  • -
Comments
xyzpdq1 xyzpdq1
Favorite

That's Swell, Sally. Pass the Harlot Salad.

advice oral sex vintage We Are Dating - 5148562432
By xyzpdq1
  • -
  • Vote
  • -
Comments
Advertisement
Dating Fails Dating Fails
Favorite

I've Never Wanted to Visit the Dentist So Badly Before

Sexy Ladies dentist ads funny vintage pin up - 8387067136
Via Joecooool418
  • -
  • Vote
  • -
Comments
Dating Fails Dating Fails
Favorite

Old Advertising Was Naughty!

innuendo funny naughty vintage WD-40 dating - 8376018176
Via Zippy225
  • -
  • Vote
  • -
Comments
Dating Fails Dating Fails
Favorite

Ye Olde Laytex Condomes

birth control cork vintage We Are Dating wood - 5064263680
By Unknown
  • -
  • Vote
  • -
Comments
Advertisement
Dating Fails Dating Fails
Favorite

This Tactic Used to Work All the Time Back in the Day

cars vintage retro pickup lines - 7963962368
By Unknown
  • -
  • Vote
  • -
Comments
School of Fail School of Fail
Favorite

A Guide for Men in the 50s (Probably Still Useable)

men dating advice funny vintage wtf - 8252380928
Via Dating Tips
  • -
  • Vote
  • -
Comments
Dating Fails Dating Fails
Favorite

If He Poked You First...

facebook facebook friends gum vintage We Are Dating - 5429727488
By bomullshode
  • -
  • Vote
  • -

"Baby, I care too much about our relationship to ruin it with Facebook."

Comments
Advertisement
Dating Fails Dating Fails
Favorite

No Hand-Holding Until Marriage, Harlot

Ad flirting ruined victorian vintage We Are Dating - 5227184128
By Unknown
  • -
  • Vote
  • -
Comments
Dating Fails Dating Fails
Favorite

You Know, I Never Thought of That

birthday comic gift roses vintage We Are Dating - 5177747712
Via reddit.com
  • -
  • Vote
  • -

Ooooh, but with the thorns? OUCH. CRINGE. SHUDDER. NO.

Comments
xyzpdq1 xyzpdq1
Favorite

Good Morning! Time to Gather Up Your Floor-Strewn Clothes!

morning vintage waking up walk of shame We Are Dating - 5407447552
By xyzpdq1
  • -
  • Vote
  • -
Comments
Advertisement
xyzpdq1 xyzpdq1
Favorite

Keep Working at It

comics phrasing funny vintage - 8184141056
By xyzpdq1
  • -
  • Vote
  • -
Comments
Dating Fails Dating Fails
Favorite

Dating Dos and Don'ts

Via Old Time TV
  • -
  • Vote
  • -
Comments
xyzpdq1 xyzpdq1
Favorite

Perfectly Legal, Too

50s demotivational kidnapping marriage vintage We Are Dating wedding - 5156924160
By xyzpdq1
  • -
  • Vote
  • -

Women: They've come a long way since the '50s.

Comments
Advertisement
Dating Fails Dating Fails
Favorite

Damn Mickey, That's Raunchy

now that's some sexy mickey milk
Via Ardorouseyes
  • -
  • Vote
  • -
Comments
Dating Fails Dating Fails
Favorite

Now That's Some Pickup Advice

old timey funny vintage pickup lines - 8243887104
Via No Bromo
  • -
  • Vote
  • -
Comments